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Determination of Amines Using 2-(11H-benzo[a]carbazol-11-yl) Ethyl Chloroformate (BCEC-Cl) as Labeling Reagent by HPLC With Fluorescence Detection and Identification With APCI/MS

Determination of Amines Using 2-(11H-benzo[a]carbazol-11-yl) Ethyl Chloroformate (BCEC-Cl) as Labeling Reagent by HPLC With Fluorescence Detection and Identification With APCI/MS

Jinmao You, Wenchen Zhao, Lingjun Liu, Xianen Zhao, Yourui Suo, Honglun Wang, Yulin Li, Chenxu Ding

Talanta. 2007 May 15;72(3):914-25.

PMID: 19071704

Abstract:

A pre-column derivatization method for the sensitive determination of amines using a labeling reagent 2-(11H-benzo[a]-carbazol-11-yl) ethyl chloroformate (BCEC-Cl) followed by high-performance liquid chromatography with fluorescence detection has been developed. Identification of derivatives was carried out by LC/APCI/MS in positive-ion mode. The chromophore of 1,2-benzo-3,4-dihydrocarbazole-9-ethyl chloroformate (BCEOC-Cl) reagent was replaced by 2-(11H-benzo[a]-carbazol-11-yl) ethyl functional group, which resulted in a sensitive fluorescence derivatizing reagent BCEC-Cl. BCEC-Cl could easily and quickly label amines. Derivatives were stable enough to be efficiently analyzed by HPLC and showed an intense protonated molecular ion corresponding m/z [M+H](+) under APCI/MS in positive-ion mode. The collision-induced dissociation of the protonated molecular ion formed characteristic fragment ions at m/z 261.8 and m/z 243.8 corresponding to the cleavages of CH(2)O-CO and CH(2)-OCO bonds. Studies on derivatization demonstrated excellent derivative yields over the pH 9.0-10.0. Maximal yields close to 100% were observed with three- to four-fold molar reagent excess. In addition, the detection responses for BCEC-derivatives were compared to those obtained using 1,2-benzo-3,4-dihydrocarbazole-9-ethyl chloroformate (BCEOC-Cl) and 9-fluorenyl methylchloroformate (FMOC-Cl) as labeling reagents. The ratios I(BCEC)/I(BCEOC)=1.94-2.17 and I(BCEC)/I(FMOC)=1.04-2.19 for fluorescent (FL) responses (here, I was relative fluorescence intensity). Separation of the derivatized amines had been optimized on reversed-phase Eclipse XDB-C(8) column. Detection limits calculated from 0.50pmol injection, at a signal-to-noise ratio of 3, were 1.77-14.4fmol. The relative standard deviations for within-day determination (n=11) were 1.84-2.89% for the tested amines. The mean intra- and inter-assay precision for all amines levels were <3.64% and 2.52%, respectively. The mean recoveries ranged from 96.6% to 107.1% with their standard deviations in the range of 0.8-2.7. Excellent linear responses were observed with coefficients of >0.9996.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP861881767	1,2-Benzo-3,4-dihydrocarbazole-9-ethyl-p-toluenesulfonate		861881-76-7	Price

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